Manufacture of secondary aromatic amino-alcohols



Patented Apr. 18 1933 UNITED STATES HELMUT LneEaLoraor BERLIN, GERMANY, Assrenon. To rnnnnnrcx stamens &

COMPANY, OF nn'rnorr, MICHIGAN MANUFACTURE OF SECONDARY AROMATICVAMINO-ALCOHOLS No Drawing. Application filed March 24, 1930, Serial No. 438,642, and in Germany raimaryiis, 1939i This invention refers to the manufacture of aromatic amino-alcohols and in'particular to the preparation of secondary amino-alcohols, constituting derivatives of the acetophenone, and in some parts it Constitutes an improvement of the subject matter of my U. S. application, Serial 274,667 of May 2,

1928 now pending. In this application I have described bodies of the general type (1 H (OH) .GO.CH .NHR, and from these may be derivedbodies of the type Y OO.R.NRI (A) 00114 may be obtained. Some of these reduction the type A. Inasmuch as with this treatment and in accordance with the state of the art there was a great liability of the splitting olf of the amino-group, particularly in case it assumed the a-POSitiOIl with relation to the CO-group this result could not be anticipated.

As reducing agents I may use nickel-cat alysts or catalysts of the noble metals or other known catalyzers, such as for instance amalgam of aluminium. The saponification is preferably elfected by treatment with miner: a1 acids.

Examples 1.10 grams p-ara-benzyl-oXy-w-methylbenzoyl-amino-aceto-phenone are dissolved in 200 cc. acetone, they'aremiired with 5 grams palladium-catalyzer, and; are then shaken with hydrogen. This will pause the substance to absorb hydrogen corresponding to 2 molecules of the body which causes the reduction of the ketone-group and the splitting of]? of the benzyl-group in the form of. toluylen; After the termination of the hydratation the resulting product is sucked ofl from the catalyzer, and the filtrate is evaporated to dryness in vacuo; The residue is boiled on the reflux-condenser for several hours with aqueous alcoholic hydrochloric acid. cThen the alcohol is removed in vacuo, thereontents of the container are shaken uptwice with ether and the clear, aqueous solution isrendered alkaline with ammonia. The parahydro-xy phenyl-N-methyl amino-ethanol lcrystallizes out and is converted into the hy-' drochloride by treatment with alcoholic hydrochloric acid. Melting point 155-157 (3.;

y e1 3% oi the'th o y. r

e rea io a es p ac aend ng tofthe 2. 15 grams meta benz o yl hydroxy a) methyl toluolene sulfony-l-arnino-acetophenone are dissolved in 200 cc...acetone and after adding thereto 5 grams n'ickel-catalyzer, they a Shak n it ydro en Afte h vi -ahrb dzthe a oanto hydrogen r qui ed tor th ,redu q lofmm listen -swap, the il ne 1 is suck iofiircm t e cata x ar, and the filt a eis p ratedmta uo- 'Therama n ns e due i heated or same tim mithsq eea ha e zhydr -io ac d fe the RHIPQSQ plit ing ef the be z a swup and the tamer lene-sulfonyl-group; the rea tion .liquid1- ,is treatedeeveraltime Wit r th mndthe M11 ous solution is then rendered ammoniacal. The meta-hydroxy-phenyl-N-methyl-aminoethanol-lwhich separates out is converted by treatment with alcoholic hydrochloric acid into the hydrochloride. Melting point 145 C.; yield 65% of the theoretical yield. The reaction takes place according to the following equations:

in which the two substituents of the phenyl group are in the para or meta'positionyX is V a benzyl or benzoyl group and Y a benzoyl or toluolene sulfonyl group, saponifying the product obtained b the reduction, and separating the alcohol rom the reaction mixture. 2. A method according to claim 1 in which the saponification is carried out with hydrochloric acid. V i V a 3. A method according to claim 1 in which the reduction is carried out by catalytic hydrogenation.

4. A method according to claim 1 in which the saponification is carried out at boiling temperature of the reaction mixture.

HELMUT LEGERLOTZ.

L I 11b 

